2-Methylindoline → 2-Methyl-1-{[5-(4-methylphenyl)isoxazol-4-yl]carbonyl}indoline

HRID 1446325Notes

Reaction equation

HRID 1446325 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13](Cl)=[O:14])=[CH:4][CH:3]=1.[CH3:16][CH:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18]1>ClCCl>[CH3:16][CH:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]1[C:13]([C:9]1[CH:10]=[N:11][O:12][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:14]

Participants

4

Reactant 2

HCID 233052-MethylindolineHCID 729429065-(P-tolyl)isoxazole-4-carbonyl chloride

Product 1

HCID 591701242-Methyl-1-{[5-(4-methylphenyl)isoxazol-4-yl]carbonyl}indoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-(4-methylphenyl)isoxazole-4-carbonyl chloride (10 mg, 0.045 mmol) in dichloromethane (1 mL) was added 2-methylindoline (6.6 mg, 0.050 mmol, 1.1 eq.), and the reaction mixture was stirred for 1 h. The solvent was removed, and the residue was purified by preparative reverse-phase HPLC to give the title compound. HRMS (ESI, pos. ion) m/z calcd for C20H18N2O2: 318.1368, found 318.1379.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-3f2dda9c818e411ab0aa9e82cf183c67
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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